Chloroacetyl chloride → N-Benzyl-2-chloro-N-isopropyl-acetamide

HRID 868574Notes

Reaction equation

HRID 868574 reaction equation
[CH:1]([NH:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:19][CH2:20][C:21](Cl)=[O:22]>ClCCl>[CH2:5]([N:4]([CH:1]([CH3:3])[CH3:2])[C:21](=[O:22])[CH2:20][Cl:19])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66024Isopropylbenzylamine

Product 1

HCID 2384365N-Benzyl-2-chloro-N-isopropyl-acetamideYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.00 g of N-isopropylbenzylamine and 3.74 g of triethylamine in 60 ml of dry dichloromethane was added dropwise 3.84 g of chloroacetyl chloride with stirring under ice-cooling. The mixture was heated under reflux for 2 hours. After cooling, the reaction mixture was successively washed with water, a 10% hydrochloric acid and an aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 7.67 g of N-benzyl-2-chloro-N-isopropylacetamide in an oil.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. temperatureAfter cooling
  5. washthe reaction mixture was successively washed with water
  6. dry with materiala 10% hydrochloric acid and an aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55aecb4097ee43b28ccd37542948a2ab
Source dataset
uspto-grants-1988_10
Patent number
US04780477

Reaction notes

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